8-Benzyl-3-(tert-butoxycarbonyl)-3,8-diazabicyclo[3.2.1]octane hydrochloride → tert-Butyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylate hydrochloride

HRID 1743697Notes

Reaction equation

HRID 1743697 reaction equation
[ClH:1].C([N:9]1[CH:14]2[CH2:15][CH2:16][CH:10]1[CH2:11][N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]2)C1C=CC=CC=1.[H][H]>[Pd].CO>[ClH:1].[CH:10]12[NH:9][CH:14]([CH2:15][CH2:16]1)[CH2:13][N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:11]2

Participants

5

Reactant 2

HCID 222354058-Benzyl-3-(tert-butoxycarbonyl)-3,8-diazabicyclo[3.2.1]octane hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 22235404tert-Butyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylate hydrochlorideYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on carbon (10% w/w, 500 mg) was added to a solution of 8-benzyl-3-(tert-butoxycarbonyl)-3,8-diazabicyclo[3.2.1]octane hydrochloride (16.5 g, 48.0 mmol, see step (h) above) in methanol (250 mL) under a nitrogen atmosphere at 25° C. The nitrogen atmosphere was exchanged for a hydrogen atmosphere (1 atm of pressure) and the reaction was stirred rapidly. After 4 h the stirring was stopped and the reaction was filtered through a pad of Celite®. The filtrate was concentrated in vacuo to afford an off-white solid (11.6 g). The solid was slurried in acetonitrile, collected and dried in vacuo to afford 10.5 g (86%) of the title compound.

Workup

  1. filtrationthe reaction was filtered through a pad of Celite®
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d3f10bab6df0452b985e0b20e8895027
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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